Direct (Hetero)arylation Reactions of (Hetero)arenes as Tools for the Step- and Atom-Economical Synthesis of Biologically Active Unnatural Compounds Including Pharmaceutical Targets

Renzo Rossi; Marco Lessi; Chiara Manzini; Giulia Marianetti; Fabio Bellina

doi:10.1055/s-0036-1588303

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(22): 3821-3862
DOI: 10.1055/s-0036-1588303

review

Direct (Hetero)arylation Reactions of (Hetero)arenes as Tools for the Step- and Atom-Economical Synthesis of Biologically Active Unnatural Compounds Including Pharmaceutical Targets

Autor*innen

Renzo Rossi*

^aDipartimento di Chimica e Chimica Industriale, University of Pisa, via G. Moruzzi 13, 56124 Pisa, Italy eMail: renzo371@alice.it eMail: fabio.bellina@dcci.unipi.it
Marco Lessi

^aDipartimento di Chimica e Chimica Industriale, University of Pisa, via G. Moruzzi 13, 56124 Pisa, Italy eMail: renzo371@alice.it eMail: fabio.bellina@dcci.unipi.it

^bConsorzio Interuniversitario Reattività Chimica e Catalisi (CIRCC), Via Celso Ulpiani 27, 70126, Bari, Italy
Chiara Manzini

^aDipartimento di Chimica e Chimica Industriale, University of Pisa, via G. Moruzzi 13, 56124 Pisa, Italy eMail: renzo371@alice.it eMail: fabio.bellina@dcci.unipi.it
Giulia Marianetti

^cScuola Normale Superiore, Piazza dei Cavalieri 7, 56126 Pisa, Italy
Fabio Bellina*

^aDipartimento di Chimica e Chimica Industriale, University of Pisa, via G. Moruzzi 13, 56124 Pisa, Italy eMail: renzo371@alice.it eMail: fabio.bellina@dcci.unipi.it

^bConsorzio Interuniversitario Reattività Chimica e Catalisi (CIRCC), Via Celso Ulpiani 27, 70126, Bari, Italy

Abstract

Alle Artikel dieser Rubrik

Abstract

The significant number of papers and reviews published in this last decade testifies to the utility of the transition-metal-catalyzed direct C–H (hetero)arylation reactions of (hetero)arenes as efficient and powerful tools for the step- and atom-economical, regio- and chemoselective synthesis of natural and unnatural compounds. However, no review has so far been devoted to summarizing the application of these reactions in the synthesis of biologically active compounds. This review with 341 references aims to fill this gap, providing a comprehensive picture of the transition-metal-catalyzed intra- and intermolecular direct C–H (hetero)arylation reactions of (hetero)arenes with (hetero)aryl halides or pseudohalides that have been used as key steps of syntheses of unnatural biologically relevant compounds including pharmaceutical targets, up to the end of September 2015. Attention has also been directed to provide a brief description of the biological properties of the synthesized compounds.

1 Introduction

2 Syntheses via Intramolecular Direct (Hetero)arylation of (Hetero)arene Derivatives

3 Syntheses via Intermolecular Direct (Hetero)arylation Reactions

3.1 Of Arenes

3.2 Of Five-Membered Heteroarenes with One Heteroatom

3.3 Of Five-Membered Heteroarenes with Two Heteroatoms

3.4 Of Five-Membered Heteroarenes with Three and Four Heteroatoms

3.5 Of Five-Membered Heteroarenes Fused to a Six-Membered Heteroarene

3.6 Of Five-Membered Heteroarene Moieties of Tricyclic Heteroarenes

3.7 Of Six-Membered Heteroarenes

4 Syntheses of Nitrogen-Containing Polycyclic Heteroarene via One-Pot Palladium-Catalyzed Domino Direct Arylation/N-Arylation Reactions

5 Conclusions

Key words

(hetero)arenes - transition-metal catalyst - direct (hetero)arylation - C–C bond formation - biological activity - drugs

Volltext

Referenzen

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179i Satish G, Vardhan Reddy H, Anil BS. P, Ramesh K, Kumar RU, Nageswar YV. D. Tetrahedron Lett. 2015; 56: 4950
179j Hubrich J, Himmler T, Rodefeld L, Ackermann L. ACS Catal. 2015; 5: 4089
179k Li Y, Wang J, Huang M, Wang Z, Wu Y, Wu Y. J. Org. Chem. 2014; 79: 2890
179l Khake SM, Soni V, Gonnade RG, Punji B. Dalton Trans. 2014; 14: 16084
179m Özdemir I, Gürbuz N, Kaloglu N, Dogan Ö, Kaloglu M, Bruneau C, Doucet H. Beilstein J. Org. Chem. 2013; 9: 303

For typical examples, see:

180a (Poly)halobenzenesulfonyl chlorides: Skhiri A, Beladhria A, Yuan K, Soulé J.-F, Bensalem R, Doucet H. Eur. J. Org. Chem. 2015; 4428
180b Arylsulfonyl chlorides: Zhang W, Liu F, Zhao B. Appl. Organomet. Chem. 2015; 29: 524
180c Sodium arenesulfinates: Zhu J, Chen Y, Lin F, Wang B, Huang Q, Liu L. Synlett 2015; 26: 1124
180d Aryldiazonium salts: Shin K, Park S.-W, Chang S. J. Am. Chem. Soc. 2015; 137: 8584
180e Aryltrimethylammonium triflates: Zhu F, Tao J.-L, Wang Z.-X. Org. Lett. 2015; 17: 4926
180f Benzenesulfonyl chlorides: Hfaiedh A, Yuan K, Ben Ammar H, Ben Hassine B, Soulé F, Doucet H. ChemSusChem 2015; 8: 1794
180g 2-Thiophenecarboxylic acids: Zhao S, Liu Y.-J, Yan S.-Y, Chen F.-J, Zhang Z.-Z, Shi B.-F. Org. Lett. 2015; 17: 3338
180h 2-Methoxybenzoic acids: Zhang Y, Zhao H, Zhang M, Su W. Angew. Chem. Int. Ed. 2015; 54: 3817
180i Diversely substituted aryl carboxylic acids: Zhang L, Xue X, Xu C, Pan Y, Zhang G, Xu L, Li H, Shi Z. ChemCatChem 2014; 6: 3069

For recent examples of C–H direct (hetero)arylation reactions carried out in or on water, see refs. 88a–d,f,g and:

181a Zhu Y, Bauer M, Ackermann L. Chem. Eur. J. 2015; 21: 9980
181b Singh KS, Dixneuf PH. ChemCatChem 2013; 5: 1313
181c Ackermann L, Mulzer M. Org. Lett. 2008; 10: 5043